TW209216B

TW209216B -

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Publication number: TW209216B
Authority: TW; Taiwan
Prior art keywords: meo; group; alkyl; cf3ch2; ministry
Prior art date: 1991-04-24

Application number

TW81103176A

Other languages

English (en)

Chinese (zh)

Original Assignee

Du Pont

Priority date

1991-04-24

Filing date

1992-04-22

Publication date

1993-07-11

1992-04-22 Application filed by Du Pont filed Critical Du Pont

1993-07-11 Application granted granted Critical

1993-07-11 Publication of TW209216B publication Critical patent/TW209216B/zh

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239000000460 chlorine Substances 0.000 claims description 398
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 388
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 213
150000001875 compounds Chemical class 0.000 claims description 184
-1 2-quinazolinyl Chemical group 0.000 claims description 155
239000007789 gas Substances 0.000 claims description 68
125000000217 alkyl group Chemical group 0.000 claims description 67
229910052739 hydrogen Inorganic materials 0.000 claims description 66
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
239000001257 hydrogen Substances 0.000 claims description 64
238000000034 method Methods 0.000 claims description 62
229910052736 halogen Inorganic materials 0.000 claims description 37
150000002367 halogens Chemical class 0.000 claims description 37
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
230000002079 cooperative effect Effects 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 30
125000004076 pyridyl group Chemical group 0.000 claims description 29
125000002541 furyl group Chemical group 0.000 claims description 26
150000002431 hydrogen Chemical group 0.000 claims description 25
125000001188 haloalkyl group Chemical group 0.000 claims description 23
229910052740 iodine Inorganic materials 0.000 claims description 22
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
229910052751 metal Chemical class 0.000 claims description 13
239000002184 metal Chemical class 0.000 claims description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
206010041349 Somnolence Diseases 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
239000004094 surface-active agent Substances 0.000 claims description 8
150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
238000011049 filling Methods 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
102000040350 B family Human genes 0.000 claims description 6
108091072128 B family Proteins 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
230000000844 anti-bacterial effect Effects 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
229910052704 radon Inorganic materials 0.000 claims description 5
SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical group [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
210000004268 dentin Anatomy 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004306 triazinyl group Chemical group 0.000 claims description 4
DMLIELSNEKKRJX-UHFFFAOYSA-N 2-(5-ethyl-6-phenyl-4,5-dihydro-3h-pyridazin-2-yl)-4,6-dimethylpyrimidine Chemical compound CCC1CCN(C=2N=C(C)C=C(C)N=2)N=C1C1=CC=CC=C1 DMLIELSNEKKRJX-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
235000013336 milk Nutrition 0.000 claims description 3
239000008267 milk Substances 0.000 claims description 3
210000004080 milk Anatomy 0.000 claims description 3
125000002757 morpholinyl group Chemical group 0.000 claims description 3
125000002755 pyrazolinyl group Chemical group 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
229910052720 vanadium Inorganic materials 0.000 claims description 3
CJLLBCZQOLAETA-UHFFFAOYSA-N 2-[6-(4-ethylphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-4,6-dimethylpyrimidine Chemical compound C1=CC(CC)=CC=C1C1=NN(C=2N=C(C)C=C(C)N=2)CCC1 CJLLBCZQOLAETA-UHFFFAOYSA-N 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000004599 antimicrobial Substances 0.000 claims description 2
230000001276 controlling effect Effects 0.000 claims description 2
150000004696 coordination complex Chemical class 0.000 claims description 2
238000009434 installation Methods 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims 4
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 3
ZGDDDFRIWCHTCX-UHFFFAOYSA-N 4,6-dimethyl-2-[6-(4-methylphenyl)-4,5-dihydro-3h-pyridazin-2-yl]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NN(C=2N=C(C)C=C(C)N=2)CCC1 ZGDDDFRIWCHTCX-UHFFFAOYSA-N 0.000 claims 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
230000000845 anti-microbial effect Effects 0.000 claims 2
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 2
JOLKIYZDRMAYTK-UHFFFAOYSA-N 2-[6-(3,4-dimethylphenyl)-4,5-dihydro-3h-pyridazin-2-yl]-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N2N=C(CCC2)C=2C=C(C)C(C)=CC=2)=N1 JOLKIYZDRMAYTK-UHFFFAOYSA-N 0.000 claims 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
239000004215 Carbon black (E152) Substances 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
208000031888 Mycoses Diseases 0.000 claims 1
125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
150000001924 cycloalkanes Chemical class 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
230000002538 fungal effect Effects 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
239000003701 inert diluent Substances 0.000 claims 1
229910021645 metal ion Inorganic materials 0.000 claims 1
125000006682 monohaloalkyl group Chemical group 0.000 claims 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
238000012856 packing Methods 0.000 claims 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
150000003222 pyridines Chemical class 0.000 claims 1
229910052705 radium Inorganic materials 0.000 claims 1
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical group [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims 1
210000003296 saliva Anatomy 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 description 171
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 119
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 107
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 72
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 63
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 44
238000012360 testing method Methods 0.000 description 39
239000000243 solution Substances 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
239000002904 solvent Substances 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 20
238000005481 NMR spectroscopy Methods 0.000 description 20
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
239000000725 suspension Substances 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 18
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 18
239000007787 solid Substances 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 18
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 17
201000010099 disease Diseases 0.000 description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
238000007639 printing Methods 0.000 description 15
125000001624 naphthyl group Chemical group 0.000 description 14
239000000126 substance Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
230000008569 process Effects 0.000 description 13
239000000047 product Substances 0.000 description 13
241000196324 Embryophyta Species 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
239000002253 acid Substances 0.000 description 10
239000012298 atmosphere Substances 0.000 description 10
239000002585 base Substances 0.000 description 10
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 10
150000002576 ketones Chemical class 0.000 description 10
239000002245 particle Substances 0.000 description 10
239000000052 vinegar Substances 0.000 description 10
235000021419 vinegar Nutrition 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000000304 alkynyl group Chemical group 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
244000052769 pathogen Species 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000011592 zinc chloride Substances 0.000 description 9
235000005074 zinc chloride Nutrition 0.000 description 9
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 9
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
125000004414 alkyl thio group Chemical group 0.000 description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 8
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
229910021578 Iron(III) chloride Inorganic materials 0.000 description 7
238000005516 engineering process Methods 0.000 description 7
239000008187 granular material Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
239000007921 spray Substances 0.000 description 7
239000002023 wood Substances 0.000 description 7
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 6
POAGKVOCGVLWPL-UHFFFAOYSA-N 4,6-dimethyl-2-(6-phenyl-4,5-dihydro-3h-pyridazin-2-yl)pyrimidine Chemical compound CC1=CC(C)=NC(N2N=C(CCC2)C=2C=CC=CC=2)=N1 POAGKVOCGVLWPL-UHFFFAOYSA-N 0.000 description 6
229910021592 Copper(II) chloride Inorganic materials 0.000 description 6
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000004927 clay Substances 0.000 description 6
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
238000011161 development Methods 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 6
230000001717 pathogenic effect Effects 0.000 description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 6
BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 5
241000209140 Triticum Species 0.000 description 5
235000021307 Triticum Nutrition 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000012267 brine Substances 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
229960004592 isopropanol Drugs 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
229920005862 polyol Polymers 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
238000005507 spraying Methods 0.000 description 5
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 4
XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 4
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
229910021380 Manganese Chloride Inorganic materials 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
241000233622 Phytophthora infestans Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000004438 haloalkoxy group Chemical group 0.000 description 4
239000011565 manganese chloride Substances 0.000 description 4
235000002867 manganese chloride Nutrition 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000010902 straw Substances 0.000 description 4
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
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